20 Can’t Miss Events on Hilton Head Island in May

As spring slowly slips into summer, it’s the perfect time to savor everything Hilton Head Island has to offer. Make the most of this special season enjoying musical productions, family festivals and kid-friendly entertainment with this handy guide to just a few of the special events taking place in May.

1. Sister ActSister Act at the Arts Center of Coastal Carolina

April 26-May 21, 2017
Across from the entrance to Palmetto Dunes, the Arts Center of Coastal Carolina presents the divine musical comedy, Sister Act, through May 21.

Suitable for all ages, this Tony-nominated show tells the hilarious story of wannabe Las Vegas diva, Deloris, whose life takes a surprising turn when she witnesses a crime and the cops hide her in the last place anyone would think to look—a convent! For details and tickets, call (843) 842-2787.

2. Music & Taste on the Harbour

May 4, 11 & 18, 2017
Music and Taste on the HarbourThursday nights through May 18, put on your dancing shoes and slide into a spot near the Neptune Statue for Music & Taste on the Harbour. These waterside outdoor concerts from 6-9 p.m. feature Deas Guyz, Target, the Band or The Headliners with specially-priced light appetizers, wine, beer and cocktails from marina restaurants. Admission is free; donations of canned goods for The Deep Well Project are greatly appreciated. For further questions, call (843) 548-0060.

3. David Yurman Trunk Show

May 4, 2017

Forsythe JewelersMother’s Day is Sunday, May 14, 2017, and Forsythe Jewelers, which is located in The Shops at Sea Pines Center, is the perfect place to find the perfect gift for mom. Capturing the casual elegance, spirited personality and confidence of the David Yurman woman, stop by the fine jewelry store on May 4 for the David Yurman Trunk Show showcasing the designer’s spring collection from 5-7 p.m. For more information, call (843) 671-7070.

4. Water Side Walk Sale

Water Sidewalk Sale Hilton Head Shelter Cove Towne CentreMay 5-7, 2017
At Shelter Cove Towne Centre, the Water Side Walk Sale is a chance to score some great deals at a waterfront sidewalk sale. Later in the month, on May 25, the Carolina Dreamers Car Club Cruise-In will roar into the center for an evening of raffles and awards sure to delight all automotive enthusiasts. For additional details on these events, call (843) 686-3090.

5. Beer, Bacon & Music Festival

May 6, 2017
Beer, Bacon and Music Festival on Hilton Head IslandThis bacon-themed block party features many of the area’s top restaurants with live music, local breweries, full-service bars offering bacon-themed cocktails and a Kid Zone. The Island Rec. Center hosts this popular Beer, Bacon & Music Festival at Shelter Cove Community Park from 11 a.m.-5 p.m. Admission is $7; free for kids 10 and under. For further information, call (843) 681-7273.

6. Salty Dog Derby Party

May 6, 2017         
In South Beach Marina Village, they’re celebrating three decades of The Salty Dog Café with live music, special parties, good food and specialty drinks. Relax and listen to the sounds of Bruce Crichton, Trevor Harden or Dave Kemmerly performing daily on the deck or stop by wearing your best Derby hat to watch the race and enjoy Browns, Mint Juleps, and Bourbon specials during the Salty Dog Derby Party.

7. Hilton Head Island Boat Show

May 6-7, 2017
Hilton Head Island Boat Show at Windmill HarbourEach spring, the exclusive Windmill Harbour neighborhood is opened to the public for one exciting weekend. Hosted in the scenic Windmill Harbour Marina, The Hilton Head Island Boat Show, which features over 60 boats, as well as tented vendors selling marine services and lifestyle goods, is a rare chance to experience the waterfront lifestyle of Windmill Harbour. The 13th Annual Boat Show will take place on May 6 from 10 a.m. to 6 p.m. and May 7 from 10 a.m. to 4 p.m. Activities and entertainment, such as live music, clinics, games, book signings, special guests and a Kentucky Derby Cocktail Party on Saturday night, are scheduled throughout the days.

8. Salty Dog Birthday Bash

Salty Dog 30th Birthday BashMay 13, 2017
This year, Salty Dog is celebrating their 30th Birthday with a fun party for everyone! Don’t miss the excitement in South Beach with the Salty Dog 30th Birthday Bash featuring food and drink specials, as well as birthday cake and, of course, appearances by Jake! Invite your friends and bring your family to Salty Dog, one of the many Hilton Head classics on the Island.

9. All Saints Garden Tour

Hilton Head All Saints Garden TourMay 20, 217
Tour seven unique Hilton Head Island and Bluffton gardens during the 30th Annual All Saints Garden Tour from 10 a.m.-4 p.m. Stop by the church to meet with Master Gardeners, enjoy a catered lunch and shop the onsite artwork sale and garden. Don’t miss the  boutique, a bake sale and Pino Gelato cart located in the parish hall! Tickets are $35 and may be purchased online at allsaintsgardentour.com.

10. Salty Dog Preakness Party

May 20, 2017
Salty DogRace down to South Beach for the Preakness Party from 4-8 p.m. featuring a Lowcountry boil, live music, kid’s fun & games and good ol’ fashioned horse racing. Bring friends, or your whole family, and enjoy a good time around the marina. For more information, call (843) 671-7273.

11. Fiesta de Mayo

May 21, 2017
The Fiesta de Mayo returns to Shelter Cove Park with live music, a couples’ dance competition, food, cultural performances and kids’ activities hosted by “La Isla Magazine.” Admission is $5; free for kids under 10. Call (843) 681-2393 for details.

12. Italian Sunday Dinner

May 21, 2017
Italian Sunday DinnerDon’t miss the Italian Sunday Dinner at St. Francis by the Sea featuring all-you-can-eat pasta and more! Each year the Italian-American Club of Hilton Head Island hosts a highly anticipated annual fundraising community dinner in which they serve homemade meatballs and sauce, sausage, lasagnas, bruchetta and more. Last year they served more than 500 dinners and raised money to support our scholarship programs.

13. Harbour Wine & Dine

May 21, 2017
2017 Harbour Wine & Dine on Hilton Head IslandHarbour Wine & Dine brings you the year’s most elite dining experience of the year. From 5:30-10 p.m., mingle on the dock with friends, enjoy various appetizers and your choice of beer or wine. Move to the table of your choosing to indulge in the best cuisine from the leading restaurants on the Harbour. Don’t think we forgot about the after-dinner dancing on the marina to great music and entertainment while finishing up the silent auction to benefit the AFA Academy of the Lowcountry.

14. Tanger Outlets Memorial Day SaleHilton Head Tanger Outlets

May 26-29, 2017
This Memorial Day weekend, get amazing deals and the best looks of the season during Tanger Outlets Memorial Day Sale, Friday, May 26-Monday, May 29, 2017. With all kinds of stores across two centers, this opportunity is not one to opt out on. View special savings and discount offers from your favorite brand name outlet stores at tangeroutlets.com/deals.

15. Gregg Russell Memorial Weekend Concerts

Gregg RussellMay 26-28, 2017
Hilton Head Island’s very own Pied Piper, Gregg Russell, returns to Harbour Town for his 41st season of complimentary concerts under the Liberty Oak in Harbour Town starting at 8 p.m. Get there early and save grab a seat to enjoy this Hilton Head classic entertain audiences in The Sea Pines Resort. For details, call (843) 842-1979.

16. Hilton Head Island Art Festival with Craft Marketplace

2017 Hilton Head Island Art FestivalMay 27-28, 2017
More than 100 artists will display paintings, jewelry, sculpture, photography, pottery and more around Shelter Cove Harbour during the 9th Annual Hilton Head Island Art Festival with Craft Marketplace, hosted by Howard Alan Events & American Craft Endeavors. Before or after checking out the selection of fine arts and crafts at this free show, discover the many boutiques, specialty shops and delicious dining establishments scattered throughout the marina. Call (561) 746-6615 for more information about the outdoor Hilton Head Island Art Festival.

17. Shannon Tanner Returns with Harbourfest

May 27-28, 2017
On Memorial Day Weekend, family favorite Shannon Tanner kicks off his 29th season at the Shelter Cove Harbour gazebo with Harbourfest, featuring two nightly shows at 6:30 and 8:30 p.m. Cappy the Clown is also back for another season of delighting audiences with fun entertainment, face painting and balloon twisting from 6-9 p.m. Parking and admission are always free. For further details, call (843) 548-0060.

18. America Sings!

May 28, 2017
Hilton Head Choral Society's America Sings 2017An All-American tribute to our veterans and members of our Armed Forces, the Hilton Head Choral Society presents “America Sings!” at First Presbyterian Church. This annual concert includes a guest speaker and performances by community organizations, coming together to celebrate the true meaning of Memorial Day. For tickets, call (843) 341-3818.

19. Freedom 5K

May 29, 2017
Hilton Head Freedom 5kThis Memorial Day, honor those who have served in the Armed Forces by registering for the 3rd Annual Hilton Head Freedom 5K Run & Walk at Shelter Cove Towne Centre. A portion of the proceeds from this fun family event benefits the Lowcountry Foundation. For Wounded Military Heroes. To register, visit runsignup.com.

20. Sandbox at the Stables

May 29, 2017
2017 Sandbox at the StablesOn Memorial Day, saddle up and head over to Lawton Stables for the 6th Annual Sandbox at the Stables Fundraiser from 10 a.m.-2 p.m. The local children’s museum will host an afternoon of live music, family games, crafts, exhibitions, pony rides, water slides, bounce houses, concessions and more, with The Cowpoke Caper Parade at high noon and face painting by Morgan’s Mommy Facepainting People. Admission is $5; tickets for concessions and select activities are sold separately. Guests must take the Sea Pines Trolley to the event. Call (843) 842-7645 for more information.